


Loop Holes

by stonerskittles



Category: Teen Wolf (TV)
Genre: Bottom Derek Hale/Top Stiles Stilinski, Just the Tip, M/M
Language: English
Status: Completed
Published: 2015-03-13
Updated: 2015-03-13
Packaged: 2018-03-17 16:24:34
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,379
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3536135
Author URL: https://archiveofourown.org/users/stonerskittles/pseuds/stonerskittles
Summary: <blockquote class="userstuff">
              <p>They’d come to an agreement.</p>
<p>Or, the Sheriff had sat them down, looked Derek straight in the eyes and said “No sex until he’s 18.”</p>
<p>It took Stiles approximately half an hour to discover a loop hole.</p>
            </blockquote>





	Loop Holes

They’d come to an agreement.

Or, the Sheriff had sat them down, looked Derek straight in the eyes and said “No sex until he’s 18.”

Stiles, of course, had protested until he saw his father’s glare. “No sex,” he echoed, pouting a little.

The Sheriff – John, he’d said to call him – nodded before pausing and squinted his eyes suspiciously. “That means no penetration of any kind, and no  _fondling.”_

Stiles huffed, opening his mouth, but Derek got there first. “Yes, sir. We understand.” Glaring at Stiles pointedly. Stiles bit him.

Sheriff- _John –_  nodded and stood up swiftly, clapping Derek on the shoulder as he passed. “Good talk.” He scrubbed a hand over Stiles’ buzz cut briefly. “ _Be good.”_

–

It took Stiles approximately half an hour to discover a loop hole.

 

“Dad said,” he gasped against Derek’s mouth, hips stilling for a second. “Dad said we can’t penetrate each other, right?”

Derek sighed. “What have I said about mentioning other people when we do this?”

Stiles smacked his chest. “Hear me out. No penetration. So if I sit over here,” Stiles got up and sat at his desk chair, facing Derek. “And if you stay there, we can get off without breaking any rules.”

That was- kind of smart actually. “Let’s do it. You have any lube?”

Derek smiled as Stiles flailed in his hurry to pass him the plump, half full bottle. In no time, they were both undressed and Stiles was flushed, mouth open and legs spread as he fisted his erection.

Derek, on the other hand, took it slower. He teased his nipples, dragged his fingertips down his chest to run through his coarse pubic hair. He jerked himself off for a few moments, feeling Stiles’ heated gaze on him the whole time.

When he was fully hard with beads of pre-come forming at the tip, Derek twisted his body so he was on his hands and knees.

“Wha-what are you doing?” Stiles stammered as Derek coated two fingers with lube.

“Watch,” Derek grunted, letting one lubed finger circle his hole, tilting his ass up higher. He moaned quietly as the finger breached him, sinking all the way in with no resistance at all.

In the chair, Stiles began to pant. “Fuck, Der. Look at you; so beautiful. Can you add another finger for me? Just one. Would you do that for me?”

Derek did, crying out at the slight burn and Stiles had to squeeze the base of his cock tightly or he was going to come.

Stiles made his way to Derek, kneeling behind him. Gently, as if not to startle him, Stiles placed his hands on Derek’s hips. “You look so good like this,” he blurted out, making Derek’s breathing hitch.

It wasn’t something they’d ever discussed; talking dirty that is. Mostly because Stiles was a virgin, wasn’t quite sure what he liked or didn’t like yet and Derek himself hadn’t experienced that yet.

Frankly, he’s a little alarmed at how much he liked it. Heat flared through his body at Stiles’ words, made his hole clenching involuntarily with the need to just get Stiles  _in him already._

“Stiles,” he shudders, “Touch me.”

“I am touching you.” Stiles said, gripping Derek’s hips tighter to illustrate his point.

“Fuck. You know what I mean,” Derek was not above whining. His dick is drooling pre-come into Stiles’ sheets, three fingers now pumping inside him and Derek is ready.

“I’m not sure I do,” Stiles teased.

Derek growled, pulling his fingers out to grab one of Stiles’s hands and place it on his ass. Stiles rubbed the pad of one finger against his rim, slipping in slightly as Derek thrust his hips back.

Stiles tittered. “That’s against the rules, Derek.” But he continued the rubbing, slowly driving Derek insane.

“Please.” Derek squirmed in attempt to get Stiles where he wants him. “Just your fingers, please. _”_

Abruptly, Stiles pushed two fingers inside Derek, crooking them up and slightly to the left. They rubbed at his prostate and Derek was  _done._ His whole body jerks, in an attempt to get Stiles closer or away, he doesn’t know, but his legs are shaking and his balls are drawn up tight, erection an angry red.

Derek is just on the edge of coming, can feel his body tense as he moans wantonly. “Stiles! I’m-”

But then the hands are gone, and Derek is left panting and confused. “What?” He manages weakly, barely audible with his face buried in the sheets.

“I’ve decided,” Stiles says casually, as if his fingers were not just up Derek’s ass and he wasn’t  _two seconds away from coming._ “I want you to take my cock.” Said cock was grinding between his ass cheeks, leaving the skin slightly sticky with pre-come.

“Do you want my cock, Derek?”

And that just wasn’t fair. Stiles’s voice was low, slightly husky and filled with arousal. Still, Derek made an approving noise in the back of his throat, nodding almost frantically.

Stiles laughed, like he wasn’t affected at all, but Derek felt the hands on his hips tighten- almost too tightly, if he were human, he’d have bruises for days – before they left to grip at his cock, holding it steady as he pushed the head into Derek.

“Just the tip. This is all you’re allowed.”

It wasn’t enough, Derek wanted to protect. His hole was so loose and slicked up, there was no way it would be enough. Instead, Derek unclenched one of the hands twisted into the material of Stiles’ cover, spat in it and brought it to his cock, setting a torturous pace as he fucked into his hand.

Stiles rocked his hips, sliding the tip of his dick in and out of Derek slowly, revelling in the feel of Derek clenching around his cock, as if he was hungry for it.

“Stiles,” Derek says, sounding breathless. “More. I need more.”

“More?”

“Please.” He gasps.

“You’ve been so good,” Stiles coos. “You can have a little more.”

On the next thrust Stiles let half his cock press into Derek’s slick heat, emitting a deep groan when he looks down and sees his cock in Derek. His rim a dark pink, stretched tight over Stiles’s dick.

“Beautiful.” Stiles says quietly, mostly to himself.

Still, Derek mewls in reply, taking Stiles off guard by sliding his body back and taking all of his cock in. Derek lifts his head back, moaning in triumph.

Stiles laughed darkly and gripped Derek’s shoulders. “You shouldn’t have done that.”

Derek’s hips stuttered, his breath coming out harsh and uneven. Stiles’ hips snapped into Derek’s, pace rough and unrelenting. Suddenly Stiles was pulling him up so his back was to Stiles’ chest. The new angle meant that Stiles’ cock stabbed at his prostate on every thrust.

With one hand on his cock and Stiles pounding into him, Derek knows it isn’t going to be long before he came. His dick is leaking steadily now, and the head is flushed a dark red, he’s so hard it’s nearly painful.

Derek was getting louder as he gets closer to the edge, inhaling desperately and damn near wailing when Stiles pinches his nipple between two fingers. All the combination sensations is too much, and with Stiles panting in his ear, muttering curses and how he’s going to come inside Derek, plug him up so he’s still slick and loose for when they next fuck. How he wants to see Derek ride him, wants to ride Derek and-

Derek comes, lost in the image of Stiles sinking onto his cock and seeing his mouth, _Christ_ that mouth open, lips red and swollen from swallowing down Derek’s cock.

“Fucking,  _fuck_.” Stiles groans unmistakably and bites down on Derek’s neck.

After a few minutes and they’ve got their breath somewhat back, Stiles pulls out to which Derek makes a small noise of protest but doesn’t stop him. Choosing instead to move up the bed and make room for Stiles to lie next to him.

“Dad doesn’t find out about this.” Stiles states.

Derek sighed. “Stiles, what have I said-”

“Yeah, I know.” Stiles laughs and turns his back to Derek. “Now cuddle me.”

“Yes, dear.”

Derek shakes the bed with his laughter when Stiles hits him, even though he’s smiling fondly.  

**Author's Note:**

> [Tumblr](http://halereyes.tumblr.com//)


End file.
